Episode Transcript

That’s what you were saying. I said I didn’t want to do a goal-setting episode.

Sherry Walling:

I have goals. I’ll set goals.

Rob Walling:

What goals?

Sherry Walling:

I’m gonna take a nap, that’s my goal.

Rob Walling:

Your goal is to go back to sleep?

Sherry Walling:

Yeah. I’m having a really weird sleep day.

Rob Walling:

What’s going on? Yeah, you woke up and then went back to sleep. That was very odd.

Sherry Walling:

Well, I’ve been diligently working on this writing project, and I’ve been getting up at 5:30, which is a newer schedule for me. Usually I’m up at 6:30. So I did my writing, and got some good stuff done, and then I was just so tired. So I went back to sleep from 7:00 to 8:00.

Rob Walling:

That’s kind of a good way to do it, I think.

Sherry Walling:

Well, normally that’s my workout time, but I slept instead of working out.

Rob Walling:

Yeah. But you got stuff done, because by the time it was 7:40 or 7:20, you already had a bunch of stuff done, so it’s not a bad way to do it, I think.

Sherry Walling:

Since my sole ambition in life right now is to go back to sleep, what else are we gonna talk about? Because I don’t think that our listeners really will be inspired by that as a goal.

Rob Walling:

Yeah. As admirable as it is. We wanna talk about building a healthy working culture, or healthy … almost like a healthy working relationships, and so you can think of this … Originally, I think you’re trying out, building a healthy company culture and that actually sounds a little more grandiose than I think we want to get to.

I was really thinking about, even if you’re a team of two, you’re co-founders, or you have your first hire, this is an important subject to talk about. It’s like working relationships, work style, and how to do that well starting from the very first person that you’re working with.

We know most listeners of the podcast are not managing massive teams, big companies of a few hundred people, but this stuff is important whether you’re managing one person or whether you’re managing ten or 15, and that’s really what we wanna talk about today.

I think I’ve seen a lot in my career of where this has done really well, where this has not done well, and I’ve tried to borrow and be more similar to the working relationships that I’ve enjoyed, and you as well. You’ve lived through them yourself and then you’ve dealt with a lot of clients now who are seeing both sides of this coin.

Sherry Walling:

Yeah I think that’s really true. I’m also remembering when we did our co-founder series, and we talked a lot about co-founder relationships, and realizing that that kind of relationship, your work relationships, whether it’s with your co-founder, or your contractors, can really make or break your quality of life at work, as well as I think the functionality of your business.

It seems like a good thing for us to jump into. This is come up a lot for me lately in the consulting practice, where people are talking about relationships within their team that are not healthy, and are causing a lot of disarray, and also where people are talking about the kinds of relationships within their team that are sort of sustaining them through some hard times, and can be kind of a life saving. I think this is important in either direction.

Rob Walling:

Yeah. I would agree. I think that the place where it starts is who you choose to work with. If this is a co-founder you’ve chosen, if this is employee number one, if this employee number ten, hiring the right people I believe pretty firmly based on personal experience, is a huge chunk of this. I don’t know if I’ll say it’s 70% or 80%, but I think it might be … I think if you get the right people around you, people who you work well with, people who are smart, driven but humble, and are willing to work with your work style, and you’re willing to work with theirs, it’s so much easier. You don’t have to work around …

Misunderstandings, miscommunications are just going to happen so much less frequently if you start by getting the right people on the bus, is the expression that’s commonly used.

Sherry Walling:

I realize that this is a giant question, and there are many, many books written on this subject, but from your real quick version of this answer, how do you do that? What do you look for when you’re deciding whether someone is going to be the right person for your team or not?

Rob Walling:

Number one, I’m extremely picky so I take a long time to hire, and this is something when I worked for fast growing startups, that they didn’t like it. They wanted me to just pick somebody if they were technically capable, and often times that’s not going to be the perfect fit. And that’s one of the reasons that Drip grew, in terms of headcount, slower than it otherwise could have. We had money to hire more people in 2015, but we couldn’t find … It took us five months maybe to find the right senior rails developer, because technical skill is 30%, 40% of the job, and how they work with you is the rest of it.

We do a lot of conversations. We definitely do technical evaluation with a developer, with someone in support, but I would also have a lot of conversations and ask them, “How do you take criticism? What do you not like about your current job?” Trying to get certain people who are like overly negative I’ll say, or who tend to do well on the negative, or who tend to blame those around them. Even if it’s a real, real subtle undertone, you can just detect there’s negativity, and you can detect that they think that they’re right about things.

They’re never going to come out and say that in an interview, but I’m trying to pull that out of them, like “What did you not like about your previous work experience? Your co-workers? Your boss?” And certain people are just like, “You know what? I wasn’t a good fit.” They take it on themselves literally. I heard people say, “You know, I left that company because it wasn’t a good fit for me or whatever.” But then other people would say, “I left the company because they were a bunch of idiots there.” That’s a bit of a red flag.”

Sherry Walling:

Yeah. It really communicates a level of arrogance that may make it very difficult to work well with someone on a team, and like you’ve mentioned already this negligence to take responsibility for one’s own role in whatever conflict or whatever group dynamic existed. I’m right there with you.

When I was interviewing and hiring folks to work at the clinic that I worked at in Fresno, I wanted people who were humble and who were trustworthy, probably above anything else, and folks who were really team players and not someone who’s there to show off and showboat and be the smartest person in the room. That dynamic of smartest person in the room is, in my opinion, just a really terrible dynamic for any kind of collaboration, or in the case of therapy practice, any kind of emotional vulnerability that’s necessary to have good supervision.

Rob Walling:

Yeah, and I’ve talked a lot about the problem solving approach we used at Drip, and a lot of it is all of us throwing out ideas, and just trying to find the best one, and not caring about who came up with it. To get to that kind of culture, you have to hire the right people. There’s no level of education or training that you can give people that’s going to make them do that if they don’t do it naturally.

Sherry Walling:

So, let’s say you find these great people, and they are team players, and they have great ideas, and they can contribute and collaborate well without needing to take all the glory points, what do you do as someone who is managing or leading your team to create relationships that are healthy, in an ongoing and sustainable way?

Rob Walling:

So you know, that’s another big question obviously. It’s like, “How do you manage?” Which could be an entire book or whatever, but I think there’s this really interesting balance between informality and hierarchy in the sense of, I’ve seen people swing too far in either direction.

I think on a factory floor there’s a lot of hierarchy, in construction crews there’s a lot of hierarchy, and there’s typically somebody who’s aggressive, who’s driving things, and everybody hates their boss, and it’s the prototypical kind of job that nobody likes, and it can certainly be in an office environment as well.

If you swing all the way the other end, I’ve seen jobs where it’s too informal, and the managers want to be friends with the team, and I think that can work in some instances, but I think you have to be really careful. I think it’s easy to lose the ‘who’s responsible’, is what it comes down to in my mind. It’s like if you’re the founder, that’s fine. You can have drinks with your team. I’m not saying you shouldn’t do that, but at the end of the day, you as the founder are responsible for the ship, and you have to make the decisions.

You have to try to get everyone’s input, you want to get to the best decision that you can, but ultimately it’s you, or you and your co-founder who have to make that decision, and I think that not having that type of … there’s just a tiny, tiny bit of authority that I think needs to be maintained, that I think informality can sometimes blur the lines.

Sherry Walling:

I think that’s also really good for team members, or for employees or contractors too, and I think sometimes we think about this as something that’s protective to the leader, but I think it works both ways. That when there are clear roles, and it’s clear who’s in charge and whose responsibility it is to take care of health insurance, and whose responsibility it is to make decisions that people can implement, that also helps everyone else feel safe, and clear, and they’re able to do their jobs without this kind of enmeshment of friendship. I don’t know, all of the relationship complexity that comes when it’s unclear who’s leading.

Rob Walling:

Right. I would agree with that.

Sherry Walling:

And I think there can be lots of warmth and playfulness, and you can have a great time with your team, and still maintain a level of separateness that’s good for them and for you.

Rob Walling:

Another thing that I think is extremely important, and this is something that part of who I am but it’s about loyalty. I think that as a manager you need to always have every everyone’s back. Everyone on your team’s back. Examples of this are, customers who get abusive or who are really a pain in the butt, you need to be willing to fire that customer, and you’re going to take heat for it, and they’re gonna come and get you on social media, and they’re going to troll you on blah blah blah, but you cannot let customers abuse your people.

If you work at a larger company, and you have a team, and there are other managers that are doing … abuse maybe a strong word, but that are whatever, misusing your people’s time or schedule, I think that’s a big deal. I think being involved when you feel like people on your team are in some kind of peril, I think communicating that upfront and not telling people, “I have your back,” but showing them that you have their back, and if they’re going on a scary sales call, like showing up with them, or letting them know they can cancel it, or letting … There’s just this freedom that you’re going to support them in what they do.

We’ve also seen examples where somebody makes a mistake, and forgets to turn on an email course, or they put a bug into the code that brings the site down or something, and to me that’s another example of … I’ve seen managers who do not have your back, and they throw you under the bus, and it’s this feeling of a punitive work culture. I see it as the opposite, like if we make a mistake, we tend to say, “What happened here? Why did it happen? Can we fix it in the future? Let’s all learn from it.”

That’s genuinely been my attitude about it, and I think it comes off with the team. I think that if you don’t have that, people are scared to make mistakes, and they’re going to move slow. At one point early on, Derrick broke the site and I said, “Look, we’re moving fast, and we’re breaking things.” There’s this quote from Mark Zuckerberg. This is two or three years ago. It’s like, “If were moving as fast as we are, we are going to break things sometimes.”

“Shake it off. I know it sucks and we both feel bad about it, but I’m now going to get on and I’m gonna hand-email all 30 of our customers.” Which is what I did at the time, and I explained to them what had happened, why there was an email delay, and blah blah blah. So it showed that, A, I had his back, and B, I was going to the part of the dirty work in essence. He had to fix it, but I had to go in and fix it with our customers. That kind of show of of loyalty is something that I think is a way to manage well.

Sherry Walling:

It just alleviates a lot of anxiety when people aren’t afraid to make mistakes, when people are afraid that they’re going to get blamed for being uncertain or unsure, that they have the freedom to ask for help, they have the freedom to say right away, “Oh my gosh. Hey, I did this, it went badly, help me out.”

In the kind of cultures that I’ve seen where that isn’t allowed, there’s so much anxiety and like you said, the fear of action that makes you move more slowly, but also degrades any sense of trust, and the sense in which you as a team are in it together, you’re all working toward a common goal. I think that’s what makes a great team, is that you’re all motivated, you’re all driven, and you have a clear sense of the goal in front of you, and everybody is contributing their piece to get that done.

Rob Walling:

Yeah, that’s right.

Sherry Walling:

And certainly, the loyalty, the sense in which you as a leader are ultimately the servant of everyone else saying, “I’ve got your back. I’ll fix it for you. I will make it possible for you to do your job in any way that I can.” Then that really pushes that healthy culture forward.

Rob Walling:

That’s right, but I think the danger is, you could swing too far the other way. Imagine if somebody crashed the site, and you came in and you’re like, “Hey. There’s no big deal, no problem.” But it is a big deal, and it is a problem, and I think you need to find that balance if you don’t minimize it, because then people don’t believe you. You can’t say things that just aren’t true. Just because you say them doesn’t make them true.

There’s a balance between minimizing it on one side, and then penalizing people on the other side and being in the middle somewhere, and being like, “Hey, okay. Yeah, this is a big deal it’s going to fix.” And then just powder effect. “Let’s look at this, and let’s all learn from this. Is there a way that we can fix this and shake it off?”

Sherry Walling:

I remember early on in my life as a supervisor, I gave pretty clear instructions to two of the people who were working under me, and between the two of them, they misscommunicated and they botched it, and blah blah blah, and it basically didn’t get done, and it was an important thing that had to do with one of our patient safety, and the next time that I met with them and I checked in about whether they had followed up, they just hadn’t done it. They missed it.

I, in that moment, was able to say, “Look guys, I’m really angry about this. This is not acceptable. I’m really pissed, and how do we keep this from happening again?” I think I intimidated the hell out of them in that moment, but it was also really important for me to just be really upfront with how I felt so that it was all out on the table, and we did. We had a really good conversation about what went wrong, and what needed to be done, and put in a different plan in place.

They understood that what happened, that the mistake that was made was a really big deal to me, and I guaranteed that they won’t ever make that mistake again, but yet my affection and commitment to them didn’t waver at all because once we were able to express, “Hey, this was a major fail on our part, we have to do this better.” I needed to be able to say, “Look, I’m really angry about this. This is not okay. We’re really failing at our work if we’re missing these kinds of big safety issues.”

But it was a good experience for me to have something negative happen, and everybody recovered just fine, because we like each other, and we trust each other, and I know that they didn’t mean to do something stupid, and so I’m still as equally committed to them as I was at the beginning.

Rob Walling:

There’s a luxury we have of building these small teams that you don’t have if you’re building a team at a large organization. The luxury we have is that, I like to think that a lot of us, the founders, have decent instincts about people, and are fairly reasonable people, and left to our own devices assuming that we can figure out these inner personal things, that we’re going to make pretty good calls in terms of trying to balance this informality and hierarchy, and that kind of stuff.

But the nice part is, you, right there, were able to make a decision to do that, and to let them know that it was a problem, and there was no one above you yelling and screaming that made you get all rattled and have to yell and scream at these guys. There was no one. When we’ve had website outages, it is genuinely my concern, but it’s not an external force that is forcing things, or an external policy that’s …

I ran into the city of Pasadena that just killed me. I would have a team I wanted to run in a certain way, I had instincts about how to tell people what to do and how to do it, and then these external things were just handed down from two or three layers above, and they’re suddenly, “No one has these days off in the company,” or suddenly out of … just these random policies would change, and I was asked to deliver that news, and I was supposed to not tell them that it was bullshit.

That’s really hard, and that’s, again, a luxury we have in these small teams, is that we can define our culture. We don’t have someone handing down and edict that says, “You have to terminate for this, or you can’t give people these many days off in December.” Or just whatever. They were just all these crazy policies.

I remember that, when you have to enforce things that you don’t believe in, but you have to sit and act like you do, it really creates a tough … it’s a tough place to be in.

Sherry Walling:

It’s why both you and I burned out of government work.

Rob Walling:

Totally.

Sherry Walling:

Sadly.

Rob Walling:

Seven months I lasted at City of Pasadena, and it-

Sherry Walling:

I lasted a little bit longer, but …

Rob Walling:

It was almost purely because of that. I actually liked a lot of the people I worked with, but that kind of stuff killed me.

I think wrapping up the topic on the second or third bullet, and it’s managing well, I think we’ve already explained why having some hierarchy is good. Having a totally flat structure where no one’s in charge, I think could create some chaos, some uncertainty. I think team members actually like to have that, so there’s someone to go to, to ask questions and help codify some decisions, and I think hierarchy, and then some structure. Not a ton of structure, especially for small in terms of …

When I think of structure, I think of a lot of process, a lot of how you do things, a lot of meetings. I’ve seen teams of ten people have ten hours of meetings a week or something, and I was just like, ‘No, no, no. You can’t do that and still get work done.” But some structure, a little bit of structure, I think is … At this early phase, you need some standards like, “Hey, don’t slack developers during the day unless it’s urgent. Or don’t slack anyone during the day unless it’s urgent.”

I’m making up some stuff, but these are certain policies of things or structures that we’ve tried to put in place, that help keep the team running well.

Sherry Walling:

I think that also helps create a culture of professionalism, and again I’m all for joking around and having a good time, and meeting for drinks every now and then, but I think, especially in the day in and day out of work, that some expectation of professional conduct is really important in terms of both preserving the sense that everybody feels respected, and that you could have some diversity in a team, and there’s a level of interacting with each other, or a level of structure that protects everybody from either being heard, and having these time wasting personnel issues, and protect people from their time being wasted by not having the structures in place that protect people from endless numbers of sarcastic slacks being passed around all day.

Rob Walling:

Right. And if you’re hiring the right people, they hate having their time wasted. Like the right people. Again, “right” is like in quotes as we said earlier, like you’re getting the right people on the bus. They’re motivated to get their work done. They want to ship. they get the dopamine rush from shipping a feature of their developer, or maybe shipping a blog post if they’re your marketer, or shipping a new ad campaign.

The distractions can be fun for a minute or two and then … I found that the best teams I work on really are heads down most of the time. Even when no one’s looking, and if someone’s in there joking or wasting time, it irritates you. It’s like, “I have work to do. Why aren’t you working?”

Sherry Walling:

It strikes me that you’re talking about … at least in the psychological literature, we talk about intrinsic versus extrinsic motivation. There are some people the show up to work because they are motivated to get things done, and they don’t want their time wasted and they’re built that way. It’s intrinsic.

Then there are other folks who are more externally motivated by trinkets, and rewards, and stickers on a starred chart …

Rob Walling:

Carrots and sticks?

Sherry Walling:

Yes. Yes. Carrots and sticks. How do you think about cultivating intrinsic motivation? Which I realize it’s sort of a dumb question because intrinsic is intrinsic. It’s not cultivated. But you are doing something to preserve it or protect it in somebody who’s managing well. So assuming you have the right people, and they’re all … they’ll show up ready to work, and they’re intrinsically motivated, how do you keep that flowing well in the course of a work day?

Rob Walling:

That is a really good question. The first thing is, yeah, you have to find people that are intrinsically motivated, and this is another big piece that I try to screen for when I’ve been hiring for the past 15 years frankly. Are they going to be intrinsically motivated? Then once you have them, then you need to let them run wild.

I used to say in our job description, “We like hiring really smart people and then getting out of their way.” That’s how I feel about it. You have to remove the obstacles from them getting their gig done. So if you hire a developer, I try to remove distractions, I try to buy them the best computer that we can possibly afford with two 24 inch monitors, which is what everybody on my team has. These are all things that just makes your work life that much easier, that much better.

I try to protect them from from distractions and interruptions, and allow them to to ship code as soon as they can. I will also just ask people straight up like, “Do you need more challenging work?” A recent hire, they started with this in the past month or two, it’s fantastic. He came up to me a week or two in, and he’s like, “Who has the log in to the knowledge base?” And I said, “I can get you one. What do you need?” He said, “I found an error. Who should fix it?” And I was like, “Well, do you want to?” And he was like, “Absolutely.”

It was like he was coming to me because he wanted to make something right, and he was a little bit tentative, he didn’t want to like overstep boundaries, he felt somebody owned the knowledge base, and that he was going to be overstepping, but it’s like, “No. You go do this.”

Then after two or three weeks, he said, “Can you just start having all new developer tickets assigned to me?” He was coming to me to tell me that, and that tells me he’s intrinsically motivated, and I keep asking him, “How can we get out of your way? How can we get you .. what else do you need?” And he’s like, “I’d love a task like this.” He’s out there asking.

Maybe that’s not everyone. Everyone doesn’t necessarily come to you and ask for these things, but really, is like clearing out any roadblocks that could potentially get in the way of basically what they should be doing on a day to day basis. You might hear or refer to it like a zone of genius, I just think of it as the thing that, that person really wants to do and is really good at. How can you try to remove everything else from the plate?

Another thing with intrinsic and extrinsic motivation, I listen to … there’s an audio book and it’s actually a take-down piece of Hub Spot unfortunately. Of course, Dharmesh, he was a colleague of mine, who’s the co-founder of Hub Spot, the book is called “Disrupted”, and it’s about a guy in his 50s who winds up going to work for Hub Spot, and there’s a bunch of young people working there, and then he doesn’t like the company culture. To be honest a lot of stuff he says, I disagree with in the book, but one thing he points out was how much hype there was, and how he felt like people were being extrinsically motivated by, like you said, sticker chart type stuff.

It was really poignant, the comments he made, and the rallies that they would have to try to get everybody hyped up about things. And I think that you need to think about this. Are you hiring intrinsically motivated people who want to get stuff done, or are you having to carrot and stick them with carrots and sticks?

Sherry Walling:

With carrots and sticks.

Rob Walling:

I allowed myself to introduce that.

Sherry Walling:

To what extent are you listening and eye-rolling your teammates? I’m old and cynical, so I just want to do my work, and I don’t need any extra bells and whistles. I want to be paid well, and I don’t want any drama, and anything beyond that, I tend to just roll my eyes, and feel like those rebellious kids sitting in the back of the high school pep rally thinking, “Wow. This is crap.”

Rob Walling:

Two bleeds in this one, and I think part of that is knowing your demographic and your generation. It’s like, “Who’s working for you?” Are you working with folks who you have an idea of what motivates them? Then do that. But if you don’t and you have to say things to motivate people, that’s a tougher job. I’m not sure, but I know how to motivate extrinsically motivated people very well. And I would recommend for most people starting software companies, probably not the route you want to go.

Sherry Walling:

Yeah. But that’s also not who you are. Back in the day in the recesses of your history, you were a code monkey, and the best thing … Is that an offensive term?

Rob Walling:

No, no, no. That’s cool.

Sherry Walling:

Okay. The best moment of your life is hitting render, go, or whatever you hit, and watching all the pieces fall into place, and it works magically … well magically from my perspective. But you’re not … at least historically like not a sales guy and not someone who is going after a bonus, or I don’t know. The thing about you is that you love seeing it work, not that you need this … I don’t use the word external again, but not that you need a sparkly shiny prize that is different than the innate satisfaction of seeing your process work well.

Rob Walling:

Yeah. The sparkly shiny prize is the feature going live. That’s the motivation and that’s a good point. That is a bias of mine. That’s who I am, and that tends to be the people who I’ve hired. I feel like our Drip team is fulfilled, including Derek and the rest of the team. It’s just filled with people like that, so maybe if you are more of an externally motivated person, that this might not … maybe you’re going to build a team with a different structure.

Sherry Walling:

I think one of the challenges is really having a good handle on the differences that are present within your team. The different personalities, the different motivations or motivators, and then also creating a team that still works fast and streamlined, but has some space for diverse voices or diverse experiences.

Rob Walling:

Yeah. It’s funny that the argument of homogeneous vs diverse teams, I know there’s been studies about how diversity can lend more opinions, and they can long term … we did better outcomes. I’m not sure how they define those. I think that having diverse opinions, and diverse folks on your team is something that’s going to be a benefit. I’ve always of strived for homogeneity in terms of motivation and work ethic, and intrinsic motivation.

When I look at teams that I’ve built or been a part of, those are the people that I have the deepest working relationships with. Are the people that want to get things done, and are really happy to be on board, and I guess respond to everything we’ve said here to a very, very light hierarchy, to a light structure, to having someone build the loyalty of a manager, and who pays that back with doing their best work.

Sherry Walling:

Well those are the essential qualities and that’s where you have to have homogeneity, that’s where you have to have shared values that you don’t have to explain to everyone, everybody’s on board. But in terms of cultural differences, and differences in experiences, that can deepen a team, but primarily people have to be motivated and have the same work value.

Rob Walling:

Right. At least those are the teams that I’ve seen work best, and I’ve worked on … I am trying to think, maybe a dozen teams give or take, maybe more than that over the past 15 years because I was on consulting teams that would switch up now and again. I’ve had really good working relationships with folks who look and act just like me, and I’ve had really good working relationships with people who look totally different, and act very different from me.

In terms of, like you said, culture or race or gender or any of these things, but the key factor that linked us was excellence. It was this desire, this intrinsic desire to ship things, to be motivated to do good work, and that’s the right people. Those are the right people that’s what you’re looking for, and if you can get them on board, and then treat them well, those are the two kickers.

Sherry Walling:

That’s it. That’s the job of the team captain. Is not getting in the way. Letting everybody do their good work, be excellent and protecting everyone’s personal integrity, making sure everyone feels respected, making sure everyone feels trusted, and nobody feels anxious or overly worried that they won’t be supported. But for everyone to know that they’re supported, that you have their back, and that they can just go and do their work.

Rob Walling:

Yeah, and you could call it building a company culture, you could call it team culture, you can call it just the work style of your team, but whatever you call it, these are the nuts and bolts of building to me what is a highly efficient, highly effective group of people who work together and respect one another and turn out a really good product.

Sherry Walling:

I have found it to be a really significant privilege to run a team. Something that I really have enjoyed, that’s been a really great learning experience for me, and it’s actually something I’m missing a lot now that I am operating on my own, and I am not working within a larger team, and I’m not supervising other people.

I think it’s something that’s a challenge, and it’s a different set of skills than most technical people innately possess, but something to really give thought and attention to and strive to be good at, both for your own personal sanity and the wellbeing of your company, but I think it also feels good to do well by other people, and it feels good to create an opportunity for people to make a good living doing something that’s interesting, and meaningful in a place or in a community of people where they’re valued and respected.

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Sherry has a unique combination of experience and education that results in an ability to completely understand what founders go through generally, crossed with their personal foibles specifically. The result is truly helpful, not regurgitated pop psychology or the “coaches” who haven’t been there before themselves.